Places to Stay

The Speakeasy Inn is a historic adults-only guesthouse in Old Town Key West, offering tropical-themed suites, a wraparound porch, and a Rum Bar featuring over 350 rums.

Matecumbe Resort is an oceanfront, family-friendly resort in Islamorada, offering fully equipped suites, a heated pool, private beach, and complimentary kayaks and bicycles.

Escape to Three Waters Resort & Marina for island luxury, ocean views, and endless adventure.Three Waters Resort & Marina, a Tribute Portfolio Resort, is a newly reimagined oceanfront destination in Islamorada, Florida, blending island charm with modern luxury.

Baker’s Cay Resort Key Largo — boutique waterfront resort with beach access, watersports, dining and family-friendly amenities in Key Largo, FL.

Gulf View Waterfront Resort offers a laid-back, Old Florida experience with spacious rooms featuring kitchenettes, an oceanfront pool, complimentary kayaks and paddleboards, and pet-friendly accommodations.

Historic charm meets vibrant Key West life steps from Hemingway House and the iconic lighthouse.

Seashell Motel & Key West Hostel is a budget-friendly, centrally located lodging offering private rooms and dorms, free Wi-Fi, on-site bike rentals, and proximity to Duval Street.

Colors on White offers vibrant, apartment-style accommodations in Old Town Key West. Each unit features a private entrance, kitchenette, and access to a pool with a cascading waterfall.

The Conch House Heritage Inn is a historic adult-only bed and breakfast located in Old Town Key West. Guests enjoy elegant accommodations, a pool, daily breakfast with mimosas, and a prime location just steps from Duval Street.

Old Town Suites is a boutique hotel in Key West featuring self-catering apartments with full kitchens, a coffee shop, and a prime location just steps from Duval Street and the Ernest Hemingway Home and Museum.

Drop Anchor Resort & Marina offers oceanfront accommodations with full kitchens, a heated pool, complimentary kayaks, paddleboards, and bicycles, all set in a tropical garden atmosphere. Ideal for couples and families seeking a relaxing Florida Keys getaway.

The Mermaid & The Alligator is an adults-only Victorian B&B in Old Town Key West, offering nine unique rooms, lush gardens, a plunge pool, and complimentary daily breakfast and happy hour.

Southernmost Beach Resort & Guesthouses is an oceanfront Key West escape featuring multiple heated pools, beachfront dining, a full-service spa, and lush tropical gardens just steps from Duval Street.

Ocean Key Resort & Spa in Key West offers luxury accommodations with Gulf views, a rooftop pool, three waterfront dining options, and a full-service spa, all located at the iconic Zero Duval Street.

The Cabana Clubis a premier private swim and beach club offering a range of amenities including a heated/cooled pool, private sandy beach, spa/whirlpool, showering facilities, full bar, and a beach shop.